One of the major issues with the date story "Wanderer" isn’t that he abandoned his date and then replaced her, it was that he never established the actual date to begin with. One could argue the girl should not have been hurt because he never clearly asked.
In this case, I think we can appropriately identify the real problem as not “Pulling the Trigger.” Do it. In one explosive move …and it’s over. You await results.
This is the biggest way to determine if you are in fact on date or hanging out: Was the Trigger Pulled? And it doesn’t matter if it was done by the boy or the girl, you should still hear the BANG.
Bad examples:
“Are you busy this weekend?”
“What are you doing [date]?”
“We should go together.”
“Maybe we can do something together sometime.”
“Do you like [insert activity]?”
“I’ll pick you up.”
...Do you hear the distinct lack of a ‘bang’? That’s because there isn’t one. In some cases, there wasn’t even a question mark. You heard it, but the other person might not have. Or worse- the other person can hear you fiddling with your gun before awkwardly trying shooting them in the face. Not good.
The Mac-Daddy of preparation questions “Are you busy?” is, ihmo, the worst and most overused way to avoid Pulling the Trigger. You are trying to respectfully ask for someone’s time- always assume they might be busy. 
Think to yourself in positive terms that of course they have plans- they are an active and popular person. It’s embarrassing to have to admit you have nothing going on in your life, don’t make someone else declare it! If they want to be with you, they will be willing to clear their schedule for you. Most likely, they do have something going on- even if they have not yet planned it. Washing their car, playing Parcheesi, eating cheetos out of their navel. It’s their business. The real question is would they rather spend that time with you?
The second major issue with a question like “Are you busy” is you are holding them hostage- threatening, but not firing yet. They still have time to negotiate or bring in the SWAT team. If the person you’re asking has any kind of sense, they will recognize what you’re trying to do and their mind starts to spin:
- Are they asking me what I think they’re asking me or am I overreacting?
- Do I play dumb?
- Will I look like a loser if I say I’m free?
- Do I have to mention my D&D game?
- Quick, I have to make something up so I can famously cancel it!
- Wait, am I busy? I have no idea if that thing is this weekend or next…
- I have another date then- I can’t say that!!!
- Anything but a direct answer until I know what they want.
But if the person really isn’t clued in, they might actually not see the potential doom and answer honestly- of course they’re busy…why do you ask? But then, are they playing dumb or not?!
A plethora of other favorable and unfavorable responses none of which constitute a real answer to your question- ‘would you go out with me?’ Are you starting to see how important Pulling the Trigger is? Without a clear answer to your question, you have no idea what they meant and you’re back to square one anyway- but with more drama layered on top. Stop the middleman in this already awkward flirtation.
Good Examples:
“I’d like to take you out [date]. Are you busy then?”
“Would you come with me to [insert activity]?”
“I have two tickets to [event], would be able to go with me?” (‘with me’ is important!!!)
“Are you free to spend an evening with me this week?”
Did you hear that? It was a crystal clean sound of a date commencing. I know it’s tough to be so direct, but the likelihood that you’ll get a direct answer is 900% more probable. Unless you’re dealing with a date ninja- they can avoid bullets no matter how close you thought the barrel was.
The thing to keep in mind about Pulling the Trigger is only use it if you want an answer. If you’ve done your prep work and you feel primed to take this person out, then you should feel ready enough to do it right. If you’re not ready, don’t ask.
In the sad case the other person doesn’t want to go out, they’ll likely say no and you should thank your stars because they are not someone you want to be with either. As we say in sales, expedite the No. If that’s the end conclusion, then you’d rather know before they cost you 30$ to listen to a lot of complaining.
And do it boldly. Not because it’s impressive when a person knows what they want (it is by the way), it’s also polite. Go ahead. They probably know what you’re up to anyway.
BANG.
Ps. Please send me your favorite lines. I’m making a compilation.
